# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ay92m
_database_code_depnum_ccdc_archive 'CCDC 1063242'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-07-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-Methyl-1-(methylsulfonyl)-3-phenyl-5-(phenylsulfonylmethyl)-1H-pyrrole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O4 S2'
_chemical_formula_sum            'C19 H19 N O4 S2'
_chemical_formula_weight         389.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1   '
_symmetry_space_group_name_Hall  '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0274(5)
_cell_length_b                   8.1297(5)
_cell_length_c                   14.6961(8)
_cell_angle_alpha                76.4330(10)
_cell_angle_beta                 74.7090(10)
_cell_angle_gamma                85.5280(10)
_cell_volume                     899.17(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5512
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8585
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8766
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3160
_reflns_number_gt                2916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.3767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3160
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9937(2) 0.5141(3) 0.83142(16) 0.0528(5) Uani 1 1 d . . .
H1A H 1.0075 0.5840 0.7675 0.079 Uiso 1 1 calc R . .
H1B H 0.9942 0.3973 0.8286 0.079 Uiso 1 1 calc R . .
H1C H 1.0871 0.5330 0.8570 0.079 Uiso 1 1 calc R . .
C2 C 0.5814(2) 0.3627(2) 0.86625(13) 0.0350(4) Uani 1 1 d . . .
C3 C 0.6413(3) 0.2042(2) 0.92493(17) 0.0511(5) Uani 1 1 d . . .
H3A H 0.5982 0.2034 0.9925 0.077 Uiso 1 1 calc R . .
H3B H 0.7653 0.1997 0.9086 0.077 Uiso 1 1 calc R . .
H3C H 0.5989 0.1077 0.9113 0.077 Uiso 1 1 calc R . .
C4 C 0.4626(2) 0.3804(2) 0.81325(12) 0.0329(4) Uani 1 1 d . . .
C5 C 0.4560(2) 0.5540(2) 0.76666(13) 0.0356(4) Uani 1 1 d . . .
H5 H 0.3852 0.6000 0.7258 0.043 Uiso 1 1 calc R . .
C6 C 0.5672(2) 0.6423(2) 0.79033(12) 0.0342(4) Uani 1 1 d . . .
C7 C 0.3578(2) 0.2471(2) 0.80276(13) 0.0336(4) Uani 1 1 d . . .
C8 C 0.2690(2) 0.1279(2) 0.88148(14) 0.0414(4) Uani 1 1 d . . .
H8 H 0.2772 0.1283 0.9434 0.050 Uiso 1 1 calc R . .
C9 C 0.1685(3) 0.0087(3) 0.86845(16) 0.0486(5) Uani 1 1 d . . .
H9 H 0.1106 -0.0711 0.9216 0.058 Uiso 1 1 calc R . .
C10 C 0.1534(3) 0.0071(3) 0.77752(16) 0.0500(5) Uani 1 1 d . . .
H10 H 0.0852 -0.0729 0.7692 0.060 Uiso 1 1 calc R . .
C11 C 0.2402(3) 0.1252(3) 0.69863(15) 0.0473(5) Uani 1 1 d . . .
H11 H 0.2306 0.1248 0.6370 0.057 Uiso 1 1 calc R . .
C12 C 0.3414(2) 0.2440(2) 0.71117(13) 0.0393(4) Uani 1 1 d . . .
H12 H 0.3994 0.3231 0.6576 0.047 Uiso 1 1 calc R . .
C13 C 0.6013(2) 0.8263(2) 0.75273(13) 0.0387(4) Uani 1 1 d . . .
H13A H 0.6464 0.8690 0.7977 0.046 Uiso 1 1 calc R . .
H13B H 0.4942 0.8869 0.7471 0.046 Uiso 1 1 calc R . .
C14 C 0.7575(2) 1.0840(2) 0.59540(13) 0.0367(4) Uani 1 1 d . . .
C15 C 0.8279(3) 1.1830(3) 0.64012(17) 0.0523(5) Uani 1 1 d . . .
H15 H 0.8739 1.1337 0.6922 0.063 Uiso 1 1 calc R . .
C16 C 0.8285(3) 1.3563(3) 0.6060(2) 0.0638(6) Uani 1 1 d . . .
H16 H 0.8744 1.4247 0.6356 0.077 Uiso 1 1 calc R . .
C17 C 0.7619(3) 1.4277(3) 0.52909(18) 0.0640(7) Uani 1 1 d . . .
H17 H 0.7647 1.5445 0.5058 0.077 Uiso 1 1 calc R . .
C18 C 0.6913(4) 1.3292(3) 0.48612(16) 0.0647(7) Uani 1 1 d . . .
H18 H 0.6453 1.3795 0.4342 0.078 Uiso 1 1 calc R . .
C19 C 0.6875(3) 1.1563(3) 0.51875(14) 0.0501(5) Uani 1 1 d . . .
H19 H 0.6385 1.0893 0.4897 0.060 Uiso 1 1 calc R . .
N1 N 0.64819(18) 0.52480(18) 0.85363(11) 0.0352(3) Uani 1 1 d . . .
O1 O 0.7715(2) 0.4506(2) 0.99780(10) 0.0564(4) Uani 1 1 d . . .
O2 O 0.7900(2) 0.74265(18) 0.90074(11) 0.0542(4) Uani 1 1 d . . .
O3 O 0.9195(2) 0.8021(2) 0.65175(12) 0.0668(5) Uani 1 1 d . . .
O4 O 0.6857(3) 0.79496(18) 0.57252(11) 0.0673(5) Uani 1 1 d . . .
S1 S 0.79790(6) 0.56507(6) 0.90614(3) 0.03977(15) Uani 1 1 d . . .
S2 S 0.75435(6) 0.86235(5) 0.63640(3) 0.04120(15) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 S1 1.746(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.362(2) . ?
C2 N1 1.415(2) . ?
C2 C3 1.496(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.420(2) . ?
C4 C7 1.482(2) . ?
C5 C6 1.347(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.416(2) . ?
C6 C13 1.488(2) . ?
C7 C8 1.390(2) . ?
C7 C12 1.393(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 S2 1.7976(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.379(3) . ?
C14 C15 1.383(3) . ?
C14 S2 1.7606(17) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 S1 1.6781(14) . ?
O1 S1 1.4205(15) . ?
O2 S1 1.4245(15) . ?
O3 S2 1.4327(16) . ?
O4 S2 1.4305(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 N1 107.51(14) . . ?
C4 C2 C3 128.41(16) . . ?
N1 C2 C3 124.03(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 107.55(15) . . ?
C2 C4 C7 127.99(15) . . ?
C5 C4 C7 124.46(15) . . ?
C6 C5 C4 110.07(15) . . ?
C6 C5 H5 125.0 . . ?
C4 C5 H5 125.0 . . ?
C5 C6 N1 106.62(15) . . ?
C5 C6 C13 125.68(16) . . ?
N1 C6 C13 127.65(16) . . ?
C8 C7 C12 118.23(16) . . ?
C8 C7 C4 122.56(16) . . ?
C12 C7 C4 119.15(15) . . ?
C9 C8 C7 120.54(18) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.60(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.54(18) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.10(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.99(17) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C6 C13 S2 110.31(12) . . ?
C6 C13 H13A 109.6 . . ?
S2 C13 H13A 109.6 . . ?
C6 C13 H13B 109.6 . . ?
S2 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C19 C14 C15 120.96(18) . . ?
C19 C14 S2 118.76(15) . . ?
C15 C14 S2 120.28(15) . . ?
C16 C15 C14 118.7(2) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 118.8(2) . . ?
C18 C19 H19 120.6 . . ?
C14 C19 H19 120.6 . . ?
C2 N1 C6 108.24(14) . . ?
C2 N1 S1 124.49(12) . . ?
C6 N1 S1 127.27(12) . . ?
O1 S1 O2 119.65(9) . . ?
O1 S1 N1 107.22(8) . . ?
O2 S1 N1 106.67(8) . . ?
O1 S1 C1 108.96(10) . . ?
O2 S1 C1 109.02(10) . . ?
N1 S1 C1 104.22(9) . . ?
O4 S2 O3 118.92(11) . . ?
O4 S2 C14 107.37(9) . . ?
O3 S2 C14 109.56(9) . . ?
O4 S2 C13 108.17(10) . . ?
O3 S2 C13 107.40(9) . . ?
C14 S2 C13 104.49(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C4 C5 0.5(2) . . . . ?
C3 C2 C4 C5 -177.13(19) . . . . ?
N1 C2 C4 C7 179.77(16) . . . . ?
C3 C2 C4 C7 2.2(3) . . . . ?
C2 C4 C5 C6 -0.3(2) . . . . ?
C7 C4 C5 C6 -179.60(16) . . . . ?
C4 C5 C6 N1 -0.1(2) . . . . ?
C4 C5 C6 C13 177.55(16) . . . . ?
C2 C4 C7 C8 47.4(3) . . . . ?
C5 C4 C7 C8 -133.45(19) . . . . ?
C2 C4 C7 C12 -135.24(19) . . . . ?
C5 C4 C7 C12 44.0(2) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C4 C7 C8 C9 178.06(17) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C4 C7 C12 C11 -177.85(16) . . . . ?
C5 C6 C13 S2 -82.4(2) . . . . ?
N1 C6 C13 S2 94.65(19) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
S2 C14 C15 C16 179.90(17) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
S2 C14 C19 C18 -179.41(17) . . . . ?
C4 C2 N1 C6 -0.5(2) . . . . ?
C3 C2 N1 C6 177.22(17) . . . . ?
C4 C2 N1 S1 179.52(13) . . . . ?
C3 C2 N1 S1 -2.7(3) . . . . ?
C5 C6 N1 C2 0.34(19) . . . . ?
C13 C6 N1 C2 -177.20(16) . . . . ?
C5 C6 N1 S1 -179.69(13) . . . . ?
C13 C6 N1 S1 2.8(3) . . . . ?
C2 N1 S1 O1 -32.78(17) . . . . ?
C6 N1 S1 O1 147.25(15) . . . . ?
C2 N1 S1 O2 -162.09(15) . . . . ?
C6 N1 S1 O2 17.95(18) . . . . ?
C2 N1 S1 C1 82.65(16) . . . . ?
C6 N1 S1 C1 -97.32(17) . . . . ?
C19 C14 S2 O4 4.5(2) . . . . ?
C15 C14 S2 O4 -176.04(17) . . . . ?
C19 C14 S2 O3 134.97(17) . . . . ?
C15 C14 S2 O3 -45.58(19) . . . . ?
C19 C14 S2 C13 -110.22(17) . . . . ?
C15 C14 S2 C13 69.23(18) . . . . ?
C6 C13 S2 O4 58.05(15) . . . . ?
C6 C13 S2 O3 -71.46(15) . . . . ?
C6 C13 S2 C14 172.22(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.066
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane  and Hexane'
